Compounds of the saframycin-ecteinascidin series, uses, and synthesis thereof

US6686470B2 · kind B2 · utility

Assignee

• The Trustees of Columbia University in the City of New York · US

Inventors

• Samuel J. Danishefsky · New Haven, US
• Bishan Zhou · Edison, US

Key dates

• Filing date: Jan 19, 2001
• Grant date: Feb 3, 2004
• Expiry date: Feb 18, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D217/24
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the saframycin-ecteinascidin series with cytotoxic properties having the following general formula, their uses and synthesis, are disclosed: wherein R1 and R4 is H, a C1 to C4 alkyl group, or an acyl group;wherein R2 is an ether, ester, amide, or a phthalimide group; wherein R3 is ═O, OH, an ether group, an acyl group such as OC(O)Me, OC(O)Bn and OC(O)Et, or a sulfide group; wherein R5 is H, halogen, OH, an ether group, an acyl group, or an amide group; wherein R6 is ═O, OH, OCH3, CN, or an acyloxy group; wherein R7, is ═O, OH, halogen, an ether group, or an acyl group; wherein R8 and R9 are independently H, CH3, OCH3, OC2H5, CF3, halogen such as Br and F, or R8 and R9 are joined together as a methylenedioxy group, or other five or six membered ring; wherein R10 and R11 are independently CH3, OCH3, OC2H5, SCH3, or SC2H5; wherein R12 is H, a C1 to C4 alkyl group, or an acyl group; and wherein the chiral center marked * has the R or the S configuration.